Aluminum(III) Chloride → 4-Fluoro-1,3-benzothiazol-7-ol

HRID 2178663Notes

Reaction equation

HRID 2178663 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9][S:10][C:6]=2[C:5]([O:11]C)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:1][C:2]1[C:7]2[N:8]=[CH:9][S:10][C:6]=2[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 68380313HCID 68380313, compound

Product 1

HCID 683798694-Fluoro-1,3-benzothiazol-7-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-7-methoxy-1,3-benzothiazole (C13) (10.50 g, 57.30 mmol) in dichloromethane (250 mL) was added aluminum chloride (30.56 g, 229.2 mmol) in one portion at room temperature. The reaction mixture was stirred for 12 hours and additional aluminum chloride (30.56 g, 229.2 mmol) was added. After another 12 hours, the reaction mixture was poured into ice water (1.0 L). The resulting precipitate was collected by filtration, washed with water, and with 1:1 dichloromethane/hexanes to afford the title compound as a yellow solid. Yield: 6.60 g, 39.0 mmol, 68%. Melting point: 165-167° C. LCMS m/z 170.4 (M+1). 1H NMR (300 MHz, DMSO-d6) δ 6.82 (m, 1H), 7.21 (m, 1H), 9.37 (s, 1H), 10.57 (s, 1H).

Workup

  1. waitAfter another 12 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-551a3e9fbee1478889e76708b444ed41
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

Loading…